5-Nitrouracil

5-Nitrouracil Property

Melting point:

>300 °C(lit.)

Boiling point:

281.7°C (rough estimate)

Density 

1.8278 (rough estimate)

refractive index 

1.5000 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO, Water

form 

Crystalline Powder or Needles

pka

5.19±0.10(Predicted)

color 

Off-white to pale yellow

Water Solubility 

3.61g/L(25 ºC)

BRN 

10410

InChI

InChI=1S/C4H3N3O4/c8-3-2(7(10)11)1-5-4(9)6-3/h1H,(H2,5,6,8,9)

InChIKey

TUARVSWVPPVUGS-UHFFFAOYSA-N

SMILES

C1(=O)NC=C([N+]([O-])=O)C(=O)N1

CAS DataBase Reference

611-08-5(CAS DataBase Reference)

EPA Substance Registry System

5-Nitrouracil (611-08-5)

Safety

Hazard Codes 

F,C

Risk Statements 

11-34

Safety Statements 

22-24/25-45-36/37/39-26-16

WGK Germany 

2

RTECS 

UV9104545

TSCA 

Yes

HS Code 

29335990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

5-Nitrouracil Chemical Properties,Usage,Production

Uses

5-Nitrouracil is a compound useful in organic synthesis.

Chemical Properties

Off-White Solid

Uses

5-Nitrouracil (cas# 611-08-5) is a compound useful in organic synthesis.

Definition

ChEBI: 5-nitrouracil is a C-nitro compound consisting of uracil having a nitro group at the 5-position. It is functionally related to a uracil.

Synthesis

The general procedure for the synthesis of 5-nitropyrimidine-2,4(1H,3H)-dione from pyrimidine-2,4(1H,3H)-dione: Nitric acid solution (5.34 mL, 120 mmol, 70% solution) was added drop-wise to concentrated sulfuric acid (19.7 mL, 360 mmol, 98% solution) under the condition of the temperature not exceeding 50 ℃. Subsequently, pyrimidine-2,4(1H,3H)-dione (7.204 g, 60 mmol) was added to the stirred mixed acid solution in batches while controlling the reaction temperature not to exceed 50°C. The reaction mixture was heated to 55 °C and maintained for 3 h, after which it was cooled below room temperature and the reaction was quenched with ice water (38 mL). The resulting white precipitate was collected by filtration, washed with a small amount of ice water and dried under reduced pressure at 55 °C to afford 5-nitropyrimidine-2,4(1H,3H)-dione (8.658 g, 55.11 mmol, 92% yield) as a white solid. Product properties: decomposition temperature >288°C; thin layer chromatography Rf value 0.00 (unfolding agent ratio 1:10 ethyl acetate/hexane); IR spectrum (ZnSe pool, solid) vmax: 3142-2811 cm^-1 (medium, broad, OH/NH/CH), 1732 cm^-1 (strong, C=O), 1677 and 1624 cm^-1 (strong. NO2), 1417 cm^-1 (medium, CH), 1356 cm^-1 (medium, NO2), 1318 cm^-1 (strong, aromatic R2NH/R3N), 1234 cm^-1 (strong, -OH), 975 and 832 cm^-1 (weak, aromatic ring bending); 1H NMR (500 MHz, d6-DMSO): δ 8.84 ( 1H, single peak, 6-CH) ppm; 13C NMR (125 MHz, d6-DMSO): δ 155.5 (4-C=O), 149.8 (6-CH), 147.9 (2-C=O), 125.1 (5-CNO2) ppm.

Purification Methods

The uracil recrystallises in prisms from boiling H2O as the monohydrate and loses H2O on drying in vacuo. [UV: Brown J Chem Soc 3647 1959, Brown J Appl Chem 2 239 1952, Johnson J Am Chem Soc 63 263 1941, Beilstein 24 I 313, 24 II 171, 24 III/IV 1236.]

References

[1] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 29 - 34
[2] American Chemical Journal, 1905, vol. 33, p. 443
[3] American Chemical Journal, 1908, vol. 40, p. 31
[4] Journal of Biological Chemistry, 1908, vol. 4, p. 410
[5] Journal of the American Chemical Society, 1919, vol. 41, p. 786